Triphenylphosphine → 2-((7-Bromoquinolin-5-yloxy)methyl)nicotinamide

HRID 1402715Notes

Reaction equation

HRID 1402715 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:10]=2[CH:11]=1.O[CH2:14][C:15]1[N:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH2:19])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C>C(Cl)Cl.C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([O:12][CH2:14][C:15]2[N:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([NH2:19])=[O:18])[CH:3]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 139295182-(Hydroxymethyl)pyridine-3-carboxamideHCID 1362166197-Bromoquinolin-5-ol

Product 1

HCID 712377752-((7-Bromoquinolin-5-yloxy)methyl)nicotinamideYield 45%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 mg 7-Bromo-quinolin-5-ol, 77.5 mg of 2-(hydroxymethyl)nicotinamide 3.7, 233.5 mg of triphenylphosphine and 205 mg of Di-tertbutyl-azodicarboxylate (DBAD) were dissolved in 2.5 mL of DCM and 7.5 mL of THF under Argon at room temperature. After 14 h the precipitate was collected and dried. The mother liquor was concentrated and the formed precipitate again collected to yield 72 mg Example 22.

Workup

  1. customat room temperature
  2. customAfter 14 h the precipitate was collected
  3. customdried
  4. concentrationThe mother liquor was concentrated
  5. customthe formed precipitate again collected

Sources & evidence

ORD record
ord-bf44e5152414430c883c7962c9c0f1fd
Source dataset
uspto-grants-2014_12
Patent number
US08912173B2

Reaction notes

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